Festivals near Rutland, VT.

Bookstock 2026

• May. 15 - May 17, 2026
• The Green - Woodstock, VT USA

• Other / General

• FREE!!

Bookstock, the Vermont Festival of Words, features author readings; a huge used book sale; poetry; workshops; events for children; food; and other fes ....

50th ANNUAL ORFORD NH FLEA MARKET

• Aug. 1 - Aug 1, 2026
• Orford - Orford, VT USA

50th Annual Orford Flea Market Sponsored by the Orford Volunteer Fire Department, Inc. (non-profit organization) August 1st & 2nd, 2026 (Saturday & S ....

50th ANNUAL ORFORD NH FLEA MARKET

• Aug. 2 - Aug 2, 2026
• Annual Orford Flea Market - Orford, VT USA

50th Annual Orford Flea Market Sponsored by the Orford Volunteer Fire Department, Inc. (non-profit organization) August 1st & 2nd, 2026 (Saturday & S ....

65th Annual Art in the Park Summer Festival--applications available

• Aug. 8 - Aug 9, 2026
• Main Street Park - Rutland, VT USA

Chaffee Art Center's 65th Annual Art in the Park Summer Festival Aug 8 & 9 featuring fine artists & craft persons. Exhibitor APPLICATIONS available ww ....

New World Festival

• Sep. 6 - Sep 6, 2026
• Chandler Music Hall ~ Chandler Center for the Arts - Randolph, VT USA

• Music

• $25 - $50
• $50 - $100

Get ready for an unforgettable experience at the 34th Annual New World Festival! Vermont's premier Celtic & Québecois music festival. This vibrant c ....

Annual Ramblin' Roads Country Fest 2026

• Oct. 3 - Oct 3, 2026
• Bondville Fair - Winhall, USA

• Music

• $10 - $25

Ramblin’ Roads Country Fest – Vermont 2026 ?? Bondville Fairgrounds, Winhall VT ?? October 3, 2026 ?? Rain Date: October 4 ?? Doors open at Noon - 9pm ....

65th Annual Art in the Park Fall Festival--applications available

• Oct. 10 - Oct 11, 2026
• Main Street Park - Rutland, VT USA

Chaffee Art Center's 65th Annual Art in the Park Fall Foliage Festival Oct 10 & 11 featuring fine artists & craft persons. Exhibitor APPLICATIONS avai ....

Battenkill Fly fishing & Arts Festival

• Apr. 30 - May 3, 2026
• 3938 Vermont Rte 7a - Arlington, VT USA

• Music

• $10 - $25

Recently named a Vermont Signature Event, this is more than just a festival; it’s a homecoming for anyone who finds peace in the rhythm of the river a ....

Montpelier MudFest

• Apr. 25 - Apr 25, 2026
• Montpelier - Montpelier, VT USA

• Other / General

Saturday features the Muddy Onion Gravel Grinder. This classic Central VT event is organized by Onion River Outdoors and attracts over 700 riders. Cyc ....

Bloodshot Bill with the Tsunamibots

• Apr. 23 - Apr 23, 2026
• Charlie O's - Montpelier, VT USA

• Music

BIO Award-winning, multi-instrumentalist Bloodshot Bill has been perfecting his brand of raw rhythm & honky tonk punk for over 25 years. A true styl ....

Spring Farmers Market

• Apr. 18 - Apr 18, 2026
• Vermont State University Randolph Campus - Randolph, VT USA

• Other / General

A market of farmers, growers, bakers, artists and craftsmen located at Vermont State University (formerly Vermont Technical College). 30 Vendors. Free ....

Area 52 Unveiled: A Night to Remember

• Jan. 31 - Jan 31, 2026
• 860 Southern Vermont Arts Center Dr - MANCHESTR CTR, VT USA

• Music

• FREE!!

Come celebrate the launch of Area 52 What is Area 52? As we navigate the ever-evolving landscape of grass and hemp-derived products, it’s essential ....

Area 52: The Nexus of Possibilities

• Jan. 31 - Jan 31, 2026
• Area 52 - Rutland, VT USA

• Music

• FREE!!

Come celebrate the launch of Area 52 What is Area 52? Discover the Premier Online Dispensary: Area 52 In the rapidly evolving world of weed product ....

Area 52: A World Unveiled

• Jan. 31 - Jan 31, 2026
• Area 52 - Waterbury, VT USA

• Music

• FREE!!

Come celebrate the launch of Area 52 What is Area 52? Discover the Cosmic World of Area 52: Your Premier Destination for Legal hemp-derived delta 9 ....

Area 52: Awaken the Potential

• Jan. 31 - Jan 31, 2026
• Area 52 - Waterbury, VT USA

• Music

• FREE!!

Come celebrate the launch of Area 52 What is Area 52? Welcome to Area 52: Your Premier Destination for Legal hemp-derived delta 9 tetrahydrocannabin ....

Area 52: Open New Doors

• Jan. 31 - Jan 31, 2026
• Area 52 - Waterbury, VT USA

• Music

• FREE!!

Come celebrate the launch of Area 52 What is Area 52? Unveiling Area 52: A Pioneer in the Realm of Legal Weed and Hemp-Derived Products In the ever ....

Area 52: Beyond the Known

• Jan. 31 - Jan 31, 2026
• Area 52 - Waterbury, VT USA

• Music

• FREE!!

Come celebrate the launch of Area 52 What is Area 52? Discover the Future of Weed with Area 52 As I delve into the world of weed, I find myself fas ....

Area 52: The Leap into the Limitless

• Jan. 20 - Jan 20, 2026
• Area 52 - Waterbury, VT USA

• Music

• FREE!!

"Come celebrate the launch of Area 52 What is Area 52? Innovative Formulations Area 52’s products are not only effective but also innovative. Their ....

VINYL EVOLUTION - LIVE at the GRATEFUL DEN

• Nov. 14 - Nov 14, 2025
• The Grateful Den - Glens Falls, NY USA

• Music

Time to join VINYL EVOLUTION for a night to remember (National Pickle Night) for 3 sets of Rockin' Tunes, and enjoy the Grateful Den's Amazing Food an ....

Middlebury Car Show & Fall Festival

• Oct. 12 - Oct 12, 2025
• Triangle Park - Middlebury, VT USA

Join us in Middlebury for the 4th annual Middlebury Car Show & Fall Festival. Main Street will close to welcome 75 classic cars and trucks. Food truck ....

9th Annual Mt. Sunapee Duck Drop

• Oct. 12 - Oct 12, 2025
• Mount Sunapee Resort - Newbury, NH USA

Northcape Design Build is proud to be back for the 9th annual Duck Drop at Mount Sunapee Resort on October 12 from 10 a.m. to 2 p.m. with awards at 3 ....

Montpelier Skelly Run

• Oct. 11 - Oct 11, 2025
• Montpelier - Montpelier, VT USA

• Holiday (Halloween)
• Holiday (Other)
• Outdoor / Recreation
• Seasonal (Fall)
• Sports / Fitness

• $50 - $100
• $100 - $250

Get ready to lace up your running shoes for the most spine-tingling fun run of the year "Skelly Run"!Inspired by the beloved 12ft Halloween decoration ....

Chaffee Art Center's 64th Annual Art in the Park Fall Festival

• Oct. 11 - Oct 12, 2025
• Main Street Park - Rutland, VT USA

• Arts (Arts & Crafts)
• Community (Community / Social)
• Community (Family & Kids)
• Community (Fundraiser)
• Music

• FREE!!

64th Annual Art in the Park Fall Foliage Festival featuring fine artists and craft persons, specialty foods, kid’s activities, and musical enter ....

64th Annual Art in the Park Fall Foliage Festival

• Oct. 11 - Oct 12, 2025
• Main Street Park - Rutland, VT USA

Chaffee Art Center's 64th Annual Art in the Park Fall Foliage Festival October 11 & 12 featuring fine artists & craft persons, specialty foods, kid’s ....

Vermont Sheep & Wool Festival

• Oct. 5 - Oct 5, 2025
• Fairgrounds Road - Tunbridge, VT USA

• FREE!!
• $1 - $10

The Vermont Sheep & Wool Festival celebrates local farms and natural fibers. The event features a variety of vendors offering fleece and yarn, fiber a ....